JP4049395B2 - 酢酸ビニル触媒を調製するための二段階金添加法 - Google Patents
酢酸ビニル触媒を調製するための二段階金添加法 Download PDFInfo
- Publication number
- JP4049395B2 JP4049395B2 JP53716497A JP53716497A JP4049395B2 JP 4049395 B2 JP4049395 B2 JP 4049395B2 JP 53716497 A JP53716497 A JP 53716497A JP 53716497 A JP53716497 A JP 53716497A JP 4049395 B2 JP4049395 B2 JP 4049395B2
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- Prior art keywords
- water
- compound
- soluble
- gold
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 136
- 229910052737 gold Inorganic materials 0.000 title claims abstract description 73
- 239000010931 gold Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 72
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims abstract description 71
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title abstract description 22
- 238000002360 preparation method Methods 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 108
- 150000002344 gold compounds Chemical class 0.000 claims abstract description 73
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 53
- 229910052751 metal Inorganic materials 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 34
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- -1 alkali metal acetate Chemical class 0.000 claims abstract description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims abstract description 10
- 235000011056 potassium acetate Nutrition 0.000 claims abstract description 5
- 150000002941 palladium compounds Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- 238000001556 precipitation Methods 0.000 claims description 13
- 238000005470 impregnation Methods 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 230000003100 immobilizing effect Effects 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical compound [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 claims description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 2
- 150000002940 palladium Chemical class 0.000 claims description 2
- FOGKDYADEBOSPL-UHFFFAOYSA-M rubidium(1+);acetate Chemical compound [Rb+].CC([O-])=O FOGKDYADEBOSPL-UHFFFAOYSA-M 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims 4
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 41
- 229910000510 noble metal Inorganic materials 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 150000002736 metal compounds Chemical class 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 229920001567 vinyl ester resin Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000001569 carbon dioxide Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000001764 infiltration Methods 0.000 description 7
- 230000008595 infiltration Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000010970 precious metal Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000003570 air Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002343 gold Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 229940080262 sodium tetrachloroaurate Drugs 0.000 description 2
- 229910052596 spinel Inorganic materials 0.000 description 2
- 239000011029 spinel Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- JNBLCHLVUYMNLH-UHFFFAOYSA-N 1-acetyloxyethenyl acetate Chemical group CC(=O)OC(=C)OC(C)=O JNBLCHLVUYMNLH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- GOKCJCODOLGYQD-UHFFFAOYSA-N 4,6-dichloro-2-imidazol-1-ylpyrimidine Chemical compound ClC1=CC(Cl)=NC(N2C=NC=C2)=N1 GOKCJCODOLGYQD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- WJFCOJSJSWYSGT-UHFFFAOYSA-N OC(=O)COC(=O)CC=C Chemical compound OC(=O)COC(=O)CC=C WJFCOJSJSWYSGT-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UWIKQJCVLSOKTO-ONEGZZNKSA-N [(e)-2-acetyloxyethenyl] acetate Chemical group CC(=O)O\C=C\OC(C)=O UWIKQJCVLSOKTO-ONEGZZNKSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VOISHCNADQQELQ-UHFFFAOYSA-N ethenyl 2-acetyloxyacetate Chemical compound CC(=O)OCC(=O)OC=C VOISHCNADQQELQ-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 229910021505 gold(III) hydroxide Inorganic materials 0.000 description 1
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical compound O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 1
- MPOKJOWFCMDRKP-UHFFFAOYSA-N gold;hydrate Chemical compound O.[Au] MPOKJOWFCMDRKP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
- 229910000364 palladium(II) sulfate Inorganic materials 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0205—Impregnation in several steps
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/66—Silver or gold
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63327596A | 1996-04-16 | 1996-04-16 | |
| US08/633,275 | 1996-04-16 | ||
| US08/696,413 | 1996-08-13 | ||
| US08/696,413 US5691267A (en) | 1996-04-16 | 1996-08-13 | Two step gold addition method for preparing a vinyl acetate catalyst |
| PCT/US1997/005718 WO1997038790A1 (en) | 1996-04-16 | 1997-04-08 | A two step gold addition method for preparing a vinyl acetate catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000508580A JP2000508580A (ja) | 2000-07-11 |
| JP4049395B2 true JP4049395B2 (ja) | 2008-02-20 |
Family
ID=27091839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53716497A Expired - Fee Related JP4049395B2 (ja) | 1996-04-16 | 1997-04-08 | 酢酸ビニル触媒を調製するための二段階金添加法 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0898494B1 (tr) |
| JP (1) | JP4049395B2 (tr) |
| CN (1) | CN1090995C (tr) |
| AT (1) | ATE193844T1 (tr) |
| AU (1) | AU712296B2 (tr) |
| BR (1) | BR9708622A (tr) |
| CA (1) | CA2249326C (tr) |
| CZ (1) | CZ291511B6 (tr) |
| DE (1) | DE69702313T2 (tr) |
| ES (1) | ES2147446T3 (tr) |
| IN (1) | IN192421B (tr) |
| NO (1) | NO316996B1 (tr) |
| NZ (1) | NZ332307A (tr) |
| PL (1) | PL329443A1 (tr) |
| TR (1) | TR199802087T2 (tr) |
| WO (1) | WO1997038790A1 (tr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6034030A (en) * | 1994-02-22 | 2000-03-07 | Celanese International Corporation | Vinyl acetate catalyst preparation method |
| US5948724A (en) * | 1997-10-28 | 1999-09-07 | Celanese International Corporation | Vinyl acetate catalyst comprising metallic palladium and gold and cupric acetate |
| US5859287A (en) * | 1997-10-30 | 1999-01-12 | Celanese International Corporation | Process for preparing vinyl acetate utilizing a catalyst comprising palladium, gold, and any of certain third metals |
| TW200539941A (en) | 2003-12-19 | 2005-12-16 | Celanese Int Corp | Methods of making alkenyl alkanoates |
| UA95442C2 (ru) | 2004-12-20 | 2011-08-10 | Селаниз Интернешнл Корпорейшн | Модифицированные материалы носителей для катализаторов |
| US8227369B2 (en) | 2005-05-25 | 2012-07-24 | Celanese International Corp. | Layered composition and processes for preparing and using the composition |
| US8884052B2 (en) * | 2011-12-15 | 2014-11-11 | Celanese International Corporation | Production of diacetoxyethylene by direct acetoxylation |
| DE102012003232A1 (de) * | 2012-02-20 | 2013-08-22 | Clariant Produkte (Deutschland) Gmbh | Nachvergoldung von Pd-Au-gecoateten Schalenkatalysatoren |
| DE102012008714A1 (de) * | 2012-05-03 | 2013-11-07 | Clariant Produkte (Deutschland) Gmbh | Vorimprägnierung von Schalenkatalysatoren mit einem Acetat |
| DE102012008715A1 (de) * | 2012-05-03 | 2013-11-07 | Clariant Produkte (Deutschland) Gmbh | Herstellung von Schalenkatalysatoren in einer Beschichtungsvorrichtung |
| CN102775298A (zh) * | 2012-08-06 | 2012-11-14 | 南京林业大学 | 一种羧酸乙烯酯的制备方法 |
| CN114073985B (zh) * | 2020-08-19 | 2024-03-29 | 中国石油化工股份有限公司 | 醋酸乙烯催化剂、其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048096A (en) * | 1976-04-12 | 1977-09-13 | E. I. Du Pont De Nemours And Company | Surface impregnated catalyst |
| DE4120492A1 (de) * | 1991-06-21 | 1992-12-24 | Hoechst Ag | Verfahren zur herstellung von vinylacetat |
| US5332710A (en) * | 1992-10-14 | 1994-07-26 | Hoechst Celanese Corporation | Vinyl acetate catalyst preparation method |
| US5314858A (en) * | 1992-10-14 | 1994-05-24 | Hoechst Celanese Corporation | Vinyl acetate catalyst preparation method |
| CA2135021A1 (en) * | 1993-11-19 | 1995-05-20 | David J. Gulliver | Process for the preparation of catalysts for use in the production of vinyl acetate |
-
1997
- 1997-04-08 CZ CZ19983331A patent/CZ291511B6/cs not_active IP Right Cessation
- 1997-04-08 PL PL97329443A patent/PL329443A1/xx unknown
- 1997-04-08 CA CA002249326A patent/CA2249326C/en not_active Expired - Fee Related
- 1997-04-08 WO PCT/US1997/005718 patent/WO1997038790A1/en active IP Right Grant
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- 1997-04-08 BR BR9708622-3A patent/BR9708622A/pt not_active IP Right Cessation
- 1997-04-08 ES ES97921112T patent/ES2147446T3/es not_active Expired - Lifetime
- 1997-04-08 EP EP97921112A patent/EP0898494B1/en not_active Expired - Lifetime
- 1997-04-08 NZ NZ332307A patent/NZ332307A/en not_active IP Right Cessation
- 1997-04-08 TR TR1998/02087T patent/TR199802087T2/tr unknown
- 1997-04-08 CN CN97193880A patent/CN1090995C/zh not_active Expired - Fee Related
- 1997-04-08 JP JP53716497A patent/JP4049395B2/ja not_active Expired - Fee Related
- 1997-04-08 DE DE69702313T patent/DE69702313T2/de not_active Expired - Lifetime
- 1997-04-08 AU AU27240/97A patent/AU712296B2/en not_active Ceased
- 1997-04-10 IN IN632CA1997 patent/IN192421B/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| EP0898494A1 (en) | 1999-03-03 |
| JP2000508580A (ja) | 2000-07-11 |
| CN1090995C (zh) | 2002-09-18 |
| CZ333198A3 (cs) | 1999-08-11 |
| BR9708622A (pt) | 2000-01-04 |
| NO316996B1 (no) | 2004-07-19 |
| CZ291511B6 (cs) | 2003-03-12 |
| EP0898494B1 (en) | 2000-06-14 |
| AU712296B2 (en) | 1999-11-04 |
| AU2724097A (en) | 1997-11-07 |
| WO1997038790A1 (en) | 1997-10-23 |
| ES2147446T3 (es) | 2000-09-01 |
| PL329443A1 (en) | 1999-03-29 |
| TR199802087T2 (tr) | 1999-01-18 |
| IN192421B (tr) | 2004-04-24 |
| ATE193844T1 (de) | 2000-06-15 |
| NZ332307A (en) | 1999-10-28 |
| CA2249326C (en) | 2006-06-06 |
| NO984809L (no) | 1998-12-08 |
| DE69702313D1 (de) | 2000-07-20 |
| CN1216482A (zh) | 1999-05-12 |
| DE69702313T2 (de) | 2001-01-25 |
| NO984809D0 (no) | 1998-10-15 |
| CA2249326A1 (en) | 1997-10-23 |
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